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Cupertino Holiday Rentals

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Holiday Rentals in Cupertino

RainierADU · Spacious CRTL San Jose 1B w/crib free street prkg

2.0 star property
St. Leo's
10.0 out of 10, Exceptional, (1)
"Our stay was a short one while we were visiting our daughter who lives less than a mile away. We spent most of our time at our daughter’s house and really only slept at this property. It was very clean and well-stocked in a great neighborhood and within walking distance of a number of great eateries and small shops. "
United States
Christiane J.
RainierADU · Spacious CRTL San Jose 1B w/crib free street prkg

Kasa University-Airport Santa Clara

4.0 star property
Santa Clara
9.0 out of 10, Wonderful, (55)
"It’s really nice area and safe"
United States
Martin
The price is AU$264
includes taxes & fees
29 Dec - 30 Dec
Kasa University-Airport Santa Clara

Large suite w/ private bath steps from DT Mt View

2.0 star property
Jackson Park
The price is AU$258
includes taxes & fees
9 Dec - 10 Dec
Large suite w/ private bath steps from DT Mt View

Luxury stay near Santana Row for vacation/business

West San Jose
9.2 out of 10, Wonderful, (50)
"Host was great and very communicative during our stay! Home was clean and felt very cozy! "
United States
Gisselle
The price is AU$389
includes taxes & fees
9 Dec - 10 Dec
Luxury stay near Santana Row for vacation/business

Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

Cupertino
9.6 out of 10, Exceptional, (4)
"This property is located in a residential and quiet neighborhood with a nice park within walking distance! Great place for someone who is traveling by themselves!"
United States
Kevin
The price is AU$502
includes taxes & fees
9 Dec - 10 Dec
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

Luxury Private Bedroom steps from DT Mt View

2.0 star property
Jackson Park
The price is AU$229
includes taxes & fees
11 Dec - 12 Dec
Luxury Private Bedroom steps from DT Mt View

Suite Walking Distance To Levi`s Stadium

2.0 star property
Sunnyvale
The price is AU$379
includes taxes & fees
12 Dec - 13 Dec
Suite Walking Distance To Levi`s Stadium

Brand New! Guest House - Modern Stylish & Central

Santa Clara
10.0 out of 10, Exceptional, (42)
"Our stay was great! This was a perfect guest house for our trip! Very clean and in a good neighborhood! "
United States
Shayna C.
The price is AU$384
includes taxes & fees
12 Dec - 13 Dec
Brand New! Guest House - Modern Stylish & Central

Stunning Stylish Luxury 3BR Santa Clara Home

Santa Clara
10.0 out of 10, Exceptional, (3)
"Such a beautiful home! Will stay again!! "
United States
Aliyah G.
The price is AU$669
includes taxes & fees
9 Dec - 10 Dec
Stunning Stylish Luxury 3BR Santa Clara Home

Airy Modern 2BR/2BA - Parking + Laundry + Sleep 6

Shasta-Hanchett Park
9.8 out of 10, Exceptional, (8)
"Ideal location, walking distance from popular San Jose points of interest. House had a great layout and style. Would stay there again."
United States
Liberato M.
The price is AU$474
includes taxes & fees
19 Dec - 20 Dec
Airy Modern 2BR/2BA - Parking + Laundry + Sleep 6

Santana Row Properties #6 - Silicon Valley Getaway

San Jose
10.0 out of 10, Exceptional, (18)
"Came for a 49ers game and this was a great place to stay! The area has great shopping and restaurants. And the hosts were great!"
United States
Damien C.
The price is AU$762
includes taxes & fees
28 Dec - 29 Dec
Santana Row Properties #6 - Silicon Valley Getaway

Charming Apartment in the heart of Silicon Valley unit 3

San Jose
9.6 out of 10, Exceptional, (7)
"Good size unit, located very close to Santana Row and Valley Fair. Nice and Clean Apartment!"
United States
Alexander L.
The price is AU$287
includes taxes & fees
12 Dec - 13 Dec
Charming Apartment in the heart of Silicon Valley unit 3

Modern style Santana Row loft

2.0 star property
San Jose
9.0 out of 10, Wonderful, (2)
"The host was very responsive and attentive. Also loved the proximity to Santana Row shopping "
United States
Sue A.
The price is AU$641
includes taxes & fees
11 Dec - 12 Dec
Modern style Santana Row loft

San Jose 3b2b near DT & Tech Hub

Buena Vista
9.2 out of 10, Wonderful, (13)
"Overall impression was very "
United States
sydney m.
The price is AU$782
includes taxes & fees
21 Dec - 22 Dec
San Jose 3b2b near DT & Tech Hub

Entire 2BR Apt w/ AC/Laundry/EV in Quiet Sunnyvale

Sunnyvale West
10.0 out of 10, Exceptional, (2)
"Belle and David did there best to make sure that my family and I had a wonderful stay. We greatly appreciate there hospitality and wish them the best "
United States
Veronica D.
The price is AU$590
includes taxes & fees
1 Jan - 2 Jan 2026
Entire 2BR Apt w/ AC/Laundry/EV in Quiet Sunnyvale

Cozy, central Santa Clara escape

2.0 star property
Santa Clara
The price is AU$562
includes taxes & fees
15 Dec - 16 Dec
Cozy, central Santa Clara escape

Gourmet Kitchen + Private Front Yard + Parking

Burbank
8.0 out of 10, Very good, (14)
"The state was pleasant and as described. Property manager made everything very simple and was very responsive. Would highly recommend and would stay here again"
United States
Randy S.
The price is AU$297
includes taxes & fees
14 Dec - 15 Dec
Gourmet Kitchen + Private Front Yard + Parking

Comfy stay in Santa Clara

2.0 star property
Santa Clara
The price is AU$597
includes taxes & fees
21 Dec - 22 Dec
Comfy stay in Santa Clara

Private Guest Suite + Full Kitchen, 3 BD, Near SJC

Burbank
7.0 out of 10, Good, (7)
"It was convenient, stores and food within walking distance"
United States
Anonymous traveller
The price is AU$293
includes taxes & fees
21 Dec - 22 Dec
Private Guest Suite + Full Kitchen, 3 BD, Near SJC

Remote work, visitor's Love 4B with 2x suites /3BR- Levis, Kaiser, Great America

Santa Clara
9.6 out of 10, Exceptional, (24)
"We had such a wonderful experience here for our 1 week stay. The beds were so comfortable, the house was super clean and the kitchen had everything we needed to cook for our group. Seamless check in and our host was always ready to assist if we needed it! Would definately recommend!!!"
United States
Susan
The price is AU$653
includes taxes & fees
10 Dec - 11 Dec
Remote work, visitor's Love 4B with 2x suites /3BR- Levis, Kaiser, Great America
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cupertino Hotel Reviews

Find out more about Cupertino

Everything you need to know about Cupertino holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cupertino holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cupertino holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cupertino holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cupertino. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cupertino holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cupertino holiday rentals we have selected for you start as low as AU$264 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cupertino rentals

At Expedia, we put the best Cupertino holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cupertino rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cupertino holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cupertino. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Cupertino?

Yes, there are holiday rentals in Cupertino close to Bowlmor Lanes, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Cupertino. The live music and theatre scene are some other things you might like to check out during your trip.

What are some of the best holiday rentals that Cupertino has to offer?

Marbella Lane Triplex San Jose: This holiday home rental outside of Cupertino has cable TV and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware.

How many holiday rentals are there in Cupertino?

Expedia has 16 holiday rentals for your stay in Cupertino.

What’s there to see and do in Cupertino?

Enjoy the outdoors at Silicon Valley and Santa Cruz Mountains, or simply take in cultural attractions like McClellan Ranch Park and Cupertino Historical Society and Museum. In the wider area, you’ll find popular places such as Levi's Stadium and SAP Center at San Jose.

What are holiday rentals like in Cupertino?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cupertino. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.